Fused polycyclic heteroaromatic compound, organic thin film including compound and electronic device including organic thin film

ABSTRACT

A low-molecular-weight fused polycyclic heteroaromatic compound may have a compact planar structure in which seven or more rings are fused together, and thereby exhibits high charge mobility, and furthermore, enables the use of a deposition process or a room-temperature solution process when applied to devices, therefore realizing improved processibility. An organic thin film and electronic device may include the fused polycyclic heteroaromatic compound.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority under 37 U.S.C. §119 to Korean PatentApplication No. 10-2012-0060623 filed in the Korean IntellectualProperty Office on Jun. 5, 2012, the entire contents of which areincorporated herein by reference.

BACKGROUND

1. Field

Example embodiments relate to a fused polycyclic heteroaromaticcompound, an organic thin film including the same, and an electronicdevice including the organic thin film.

2. Description of the Related Art

In general, flat display devices, e.g., liquid crystal displays ororganic electroluminescent displays, are provided with a variety of thinfilm transistors (TFTs) to drive them. The TFT may include a gateelectrode, source/drain electrodes, and a semiconductor layer that maybe activated in response to the operation of the gate electrode. Thesemiconductor layer may include an organic semiconductor material thatis controlled by a current between the source electrode and the drainelectrode generated by an applied gate voltage.

Recently, as a material for a channel of the TFT, organic materials,e.g., pentacene or polythiophene, have been studied. In the case ofpolymer or oligomer organic materials, e.g., F8T2(poly(9,9-dioctylfluorene-co-bithiophene)) as a polythiophene-basedmaterial, and a solution process, e.g., spin casting, may be desirablyapplied. However, problems of decreased charge mobility and increasedoff-state leakage current may occur. Further, low-molecular-weightorganic materials, e.g., pentacene, may have a relatively high chargemobility of about 3.2 to about 5.0 cm²/Vs or more, but may require arelatively expensive apparatus for vacuum deposition at the time offorming a thin film. Therefore, the low-molecular-weight organicmaterial may be unsuitable for use in the preparation of a film having arelatively large area, and processibility may be undesirable.

Thus, there have been attempts to devise materials for channel layershaving increased charge mobility and improved processibility. Therelated art discloses dimeric bisbenzodithiophene, in which rings may befused in groups of three and thus increased charge mobility may berealized.

SUMMARY

Example embodiments provide a low-molecular-weight fused polycyclicheteroaromatic compound that has a compact planar structure in whichseven or more aromatic rings are fused together, and thereby exhibitshigher charge mobility, and furthermore, enables the use of a depositionprocess or a room-temperature solution process when applied to devices,therefore realizing improved processibility.

Example embodiments also provide an organic thin film including thefused polycyclic heteroaromatic compound. Example embodiments alsoprovide an electronic device including the organic thin film as acarrier transport layer.

According to example embodiments, a fused polycyclic heteroaromaticcompound may be represented by the following Chemical Formula 1.

[Chemical Formula 1]

In the above Chemical Formula 1,

Ar is a substituted or unsubstituted C₆ to C₃₀ aromatic cyclic group,

each of X¹ to X⁴ are independently one of O, S, Se, Te, N—R^(a), andCR^(b), wherein each of R^(a) and R^(b) are independently one ofhydrogen, a substituted or unsubstituted linear or branched C₁ to C₃₀alkyl group, a substituted or unsubstituted C₇ to C₃₀ arylalkyl group, asubstituted or unsubstituted C₆ to C₃₀ aryl group, a substituted orunsubstituted C₁ to C₃₀ alkoxy group, a substituted or unsubstituted C₆to C₃₀ aryloxy group (—OR¹¹, wherein R¹¹ is a substituted orunsubstituted C₆ to C₃₀ aryl group), a substituted or unsubstituted C₄to C₃₀ cycloalkyl group, a substituted or unsubstituted C₄ to C₃₀cycloalkyloxy group (−OR¹², wherein R¹² is a substituted orunsubstituted C₄ to C₃₀ cycloalkyl group), a substituted orunsubstituted C₂ to C₃₀ heteroaryl group, an acyl group (—C(═O)R¹³,wherein R¹³ is a substituted or unsubstituted C₁ to C₃₀ alkyl group), asulfonyl group (—S(═O)₂R¹⁴, wherein R¹⁴ is a substituted orunsubstituted C₁ to C₃₀ alkyl group) and a carbamate group(—NHC(═O)OR¹⁵, wherein R¹⁵ is a substituted or unsubstituted C₁ to C₃₀alkyl group),

at least one of X¹ and X² is selected from O, S, Se, Te, and N—R^(a),

at least one of X³ and X⁴ is selected from O, S, Se, Te, and N—R^(a),

each of X⁵ and X⁶ are independently one of O, S, Se, Te, N—R^(a), andCR^(b)R^(c) wherein each of R^(a) to R^(c) are independently one ofhydrogen, a substituted or unsubstituted linear or branched C₁ to C₃₀alkyl group, a substituted or unsubstituted C₇ to C₃₀ arylalkyl group, asubstituted or unsubstituted C₆ to C₃₀ aryl group, a substituted orunsubstituted C₁ to C₃₀ alkoxy group, a substituted or unsubstituted C₆to C₃₀ aryloxy group (—OR¹¹, wherein R¹¹ is a substituted orunsubstituted C₆ to C₃₀ aryl group), a substituted or unsubstituted C₄to C₃₀ cycloalkyl group, a substituted or unsubstituted C₄ to C₃₀cycloalkyloxy group (−OR¹², wherein R¹² is a substituted orunsubstituted C₄ to C₃₀ cycloalkyl group), a substituted orunsubstituted C₂ to C₃₀ heteroaryl group, an acyl group (—C(═O)R¹³,wherein R¹³ is a substituted or unsubstituted C₁ to C₃₀ alkyl group), asulfonyl group (—S(═O)₂R¹⁴, wherein R¹⁴ is a substituted orunsubstituted C₁ to C₃₀ alkyl group) and a carbamate group(—NHC(═O)OR¹⁶, wherein R¹⁵ is a substituted or unsubstituted C₁ to C₃₀alkyl group), and

each of R¹ to R⁶ are independently one of hydrogen, a halogen (—F, —Cl,—Br or —I), a substituted or unsubstituted linear or branched C₁ to C₃₀alkyl group, a substituted or unsubstituted linear or branched C₂ to C₃₀alkenyl group, a substituted or unsubstituted linear or branched C₂ toC₃₀ alkynyl group, a substituted or unsubstituted C₇ to C₃₀ arylalkylgroup, a substituted or unsubstituted C₂ to C₃₀ heteroarylalkyl group, asubstituted or unsubstituted C₂ to C₃₀ alkylheteroaryl group, asubstituted or unsubstituted C₅ to C₃₀ cycloalkyl group, a substitutedor unsubstituted C₂ to C₃₀ heterocycloalkyl group, a substituted orunsubstituted C₆ to C₃₀ aryl group, and a substituted or unsubstitutedC₂ to C₃₀ heteroaryl group.

The fused polycyclic heteroaromatic compound may be one of fusedpolycyclic heteroaromatic compounds represented by the followingChemical Formulae 1A to 1G.

In the above Chemical Formulae 1A to 1G,

X¹, X², X³, X⁴, X⁵, X⁶, R¹, R², R³, R⁴, R⁵ and R⁶ are the same as inChemical Formula 1,

each of R¹⁰⁰ to R¹⁰² are independently one of hydrogen, halogen(—F, —Cl,—Br or —I), a substituted or unsubstituted linear or branched C₁ to C₃₀alkyl group, a substituted or unsubstituted linear or branched C₂ to C₃₀alkenyl group, a substituted or unsubstituted linear or branched C₂ toC₃₀ alkynyl group, a substituted or unsubstituted C₇ to C₃₀ arylalkylgroup, a substituted or unsubstituted C₂ to C₃₀ heteroarylalkyl group, asubstituted or unsubstituted C₂ to C₃₀ alkylheteroaryl group, asubstituted or unsubstituted C₅ to C₃₀ cycloalkyl group, a substitutedor unsubstituted C₂ to C₃₀ heterocycloalkyl group, a substituted orunsubstituted C₆ to C₃₀ aryl group, and a substituted or unsubstitutedC₂ to C₃₀ heteroaryl group, and

x, y, and z are integers of 1 or 2.

In Chemical Formula 1, one of X¹ and X² and one of X³ and X⁴ may besulfur (S).

The fused polycyclic heteroaromatic compound may have an averagemolecular weight of about 350 to about 3000.

In Chemical Formula 1, an atom of each of X¹ and X⁴, and X² and X³ ispositioned symmetrically to each other.

In Chemical Formula 1, Ar is one of a substituted or unsubstitutedbenzene, a substituted or unsubstituted naphthalene, and a substitutedor unsubstituted anthracene.

In Chemical Formula 1, each of R¹ to R⁶ are independently one of asubstituted or unsubstituted linear or branched C₁ to C₃₀ alkyl group, asubstituted or unsubstituted linear or branched C₂ to C₃₀ alkenyl group,a substituted or unsubstituted linear or branched C₂ to C₃₀ alkynylgroup, a substituted or unsubstituted C₇ to C₃₀ arylalkyl group, asubstituted or unsubstituted C₂ to C₃₀ heteroarylalkyl group, asubstituted or unsubstituted C₂ to C₃₀ alkylheteroaryl group, asubstituted or unsubstituted C₅ to C₃₀ cycloalkyl group, a substitutedor unsubstituted C₂ to C₃₀ heterocycloalkyl group, a substituted orunsubstituted C₆ to C₃₀ aryl group, and a substituted or unsubstitutedC₂ to C₃₀ heteroaryl group.

According to example embodiments, an organic thin film and an electronicdevice may include the fused polycyclic heteroaromatic compound.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects will become apparent and more readilyappreciated from the following description of example embodiments, takenin conjunction with the accompanying drawings of which:

FIG. 1 is a schematic cross-sectional view of a transistor according toexample embodiments.

FIG. 2 is a schematic cross-sectional view of a transistor according toexample embodiments.

FIG. 3 shows a Maldi-MS spectrum of the compound 4 according to Example1.

FIG. 4 shows current transfer characteristics of the organic thin filmtransistor according to Example 2.

DETAILED DESCRIPTION

Example embodiments will now be described more fully with reference tothe accompanying drawings. However, it should be understood that theexamples may be embodied in many different forms and should not beconstrued as being limited to the embodiments set forth herein. Rather,these embodiments are merely provided so that this disclosure will bemore thorough and complete and will assist in fully conveying theconcept of example embodiments to those of ordinary skill in the art.Like reference numerals in the drawings denote like elements, and thustheir description in a similar drawing may be omitted for purposes ofbrevity.

It will be understood that when an element is referred to as being“connected” or “coupled” to another element, it can be directlyconnected or coupled to the other element or intervening elements may bepresent. In contrast, when an element is referred to as being “directlyconnected” or “directly coupled” to another element, there are nointervening elements present. Like numbers indicate like elementsthroughout. As used herein the term “and/or” includes any and allcombinations of one or more of the associated listed items. Other wordsused to describe the relationship between elements or layers should beinterpreted in a like fashion (e.g., “between” versus “directlybetween,” “adjacent” versus “directly adjacent,” “on” versus “directlyon”).

It will be understood that, although the terms “first”, “second”, etc.may be used herein to describe various elements, components, regions,layers and/or sections, these elements, components, regions, layersand/or sections should not be limited by these terms. These terms areonly used to distinguish one element, component, region, layer orsection from another element, component, region, layer or section. Thus,a first element, component, region, layer or section discussed belowcould be termed a second element, component, region, layer or sectionwithout departing from the teachings of example embodiments.

Spatially relative terms, such as “beneath,” “below,” “lower,” “above,”“upper” and the like, may be used herein for ease of description todescribe one element or feature's relationship to another element(s) orfeature(s) as illustrated in the figures. It will be understood that thespatially relative terms are intended to encompass differentorientations of the device in use or operation in addition to theorientation depicted in the figures. For example, if the device in thefigures is turned over, elements described as “below” or “beneath” otherelements or features would then be oriented “above” the other elementsor features. Thus, the term “below” can encompass both an orientation ofabove and below. The device may be otherwise oriented (rotated 90degrees or at other orientations) and the spatially relative descriptorsused herein interpreted accordingly.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting of exampleembodiments. As used herein, the singular forms “a,” “an” and “the” areintended to include the plural forms as well, unless the context clearlyindicates otherwise. It will be further understood that the terms“comprises”, “comprising”, “includes” and/or “including,” if usedherein, specify the presence of stated features, integers, steps,operations, elements and/or components, but do not preclude the presenceor addition of one or more other features, integers, steps, operations,elements, components and/or groups thereof.

Example embodiments are described herein with reference tocross-sectional illustrations that are schematic illustrations ofidealized embodiments (and perhaps intermediate structures) of exampleembodiments. As such, variations from the shapes of the illustrations asa result, for example, of manufacturing techniques and/or tolerances,are to be expected. Thus, example embodiments should not be construed aslimited to the particular shapes of regions illustrated herein but areto include deviations in shapes that result, for example, frommanufacturing. For example, an implanted region illustrated as arectangle may have rounded or curved features and/or a gradient ofimplant concentration at its edges rather than a binary change fromimplanted to non-implanted region. Likewise, a buried region formed byimplantation may result in some implantation in the region between theburied region and the surface through which the implantation takesplace. Thus, the regions illustrated in the figures are schematic innature and their shapes are not intended to illustrate the actual shapeof a region of a device and are not intended to limit the scope ofexample embodiments.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which example embodiments belong. Itwill be further understood that terms, such as those defined incommonly-used dictionaries, should be interpreted as having a meaningthat is consistent with their meaning in the context of the relevant artand will not be interpreted in an idealized or overly formal senseunless expressly so defined herein.

In the drawings, the thickness of layers, films, panels, regions, etc.,are exaggerated for clarity.

It will be understood that when an element such as a layer, film,region, or substrate is referred to as being “on” another element, itcan be directly on the other element or intervening elements may also bepresent. In contrast, when an element is referred to as being “directlyon” another element, there are no intervening elements present.

As used herein, the term “combination thereof” refers to a mixture, astacked structure, a composite, or an alloy.

As used herein, when a definition is not otherwise provided, the term“hetero” may refer to one including 1 to 4 heteroatoms selected from N,O, S, Si, and P. The total number of ring members may be 3 to 10. Ifmultiple rings are present, each ring is independently aromatic,saturated, or partially unsaturated, and multiple rings, if present, maybe fused, pendant, spirocyclic, or a combination thereof. The term“heterocycloalkyl group” may be at least one non-aromatic ring includinga heteroatom, and the term “heteroaryl group” may be at least onearomatic ring including a heteroatom. Non-aromatic and/or carbocyclicrings may also be present in a heteroaryl group, provided that at leastone ring is both aromatic and contains a ring member that is aheteroatom.

As used herein, when a definition is not otherwise provided, the term“alkyl group” may be a linear or branched saturated monovalenthydrocarbon group (e.g., a methyl group, an ethyl group, a propyl group,an isobutyl group, a sec-butyl group, a tert-butyl group, a pentylgroup, an iso-amyl group, and/or a hexyl group).

The term “alkenyl group” may refer to a linear or branched unsaturatedmonovalent hydrocarbon group including at least one carbon-carbon doublebond (e.g., an ethenyl group).

The term “alkynyl group” may refer to a linear or branched unsaturatedmonovalent hydrocarbon group including at least one carbon-carbon triplebond (e.g., ethynyl group).

The term “alkoxy group” may refer to an alkyl group that is linked viaan oxygen, e.g., a methoxy, an ethoxy, and a sec-butyloxy group.

The term “aryl group” may refer to a monovalent functional group formedby the removal of one hydrogen atom from one or more rings of an arene,e.g., phenyl or naphthyl. The arene may refer to a hydrocarbon having anaromatic ring, and includes monocyclic and polycyclic hydrocarbonswherein the additional ring(s) of the polycyclic hydrocarbon may bearomatic or nonaromatic.

The term “aryloxy group” may refer to an aryl group that is linked viaan oxygen, and the aryl group is the same as described above.

The “arylalkyl group” may refer to an aryl group where one hydrogen issubstituted with a lower alkylene, e.g., methylene, ethylene, and/orpropylene. For example, the “arylalkyl group” may be a benzyl group or aphenylethyl group.

The term “cycloalkyl group” may refer to a monovalent functional grouphaving one or more saturated rings in which all ring members are carbon,e.g., a cyclopentyl group and a cyclohexyl group.

The term “cycloalkenyl group” may refer to a monovalent functional groupincluding at least one ring having a carbon-carbon double bond, whereinall ring members are carbon, e.g., a cyclopentenyl group or acyclohexenyl group.

The term “cycloalkynyl group” may refer to a stabilized aliphaticmonocyclic or polycyclic functional group including at least onecarbon-carbon triple bond.

The term “heteroarylalkyl group” may refer to the alkyl group definedabove where at least one hydrogen is substituted with a heteroarylgroup.

The term “alkylheteroaryl group” may refer to the heteroaryl groupdefined above where at least one hydrogen is substituted with an alkylgroup.

As used herein, when a definition is not otherwise provided, the term“aromatic ring” refers to a functional group in which all atoms in thecyclic functional group have a p-orbital, wherein these p-orbitals areconjugated. For example, the aromatic ring may be a C₆ to C₂₀ arylgroup.

As used herein, when a definition is not otherwise provided, the term“heteroaromatic ring” refers to a functional group including aheteroatom selected from N, O, and S in a ring in which all atoms in thecyclic functional group have a p-orbital, wherein the p-orbital isconjugated. For example, the heteroaromatic ring may be a C₂ to C₂₀heteroaryl group.

As used herein, when a definition is not otherwise provided, the term“alicyclic ring” may refer to non-conjugated ring, for example, a C₃ toC₂₀ cycloalkyl group, a C₃ to C₂₀ heterocycloalkyl group, a C₃ to C₂₀cycloalkenyl group, and/or a C₃ to C₂₀ heterocycloalkenyl group.

As used herein, when a definition is not otherwise provided, the term“substituted” means that a compound or group is substituted with atleast one substituent selected independently from a halogen (—F, —Cl,—Br, or —I), a C₁ to C₃₀ linear or branched alkyl group, for example, aC₁ to C₁₀ linear or branched alkyl group, C₂ to C₃₀ linear or branchedalkenyl group, for example, a C₂ to C₁₀ linear or branched alkenylgroup, a C₂ to C₃₀ linear or branched alkynyl group, for example, a C₂to C₁₀ linear or branched alkynyl group, a C₆ to C₃₀ aryl group, forexample, a C₆ to C₁₂ aryl group, a C₂ to C₃₀ heteroaryl group, forexample, a C₂ to C₁₂ heteroaryl group, a C₃ to C₃₀ cycloalkyl group, aC₁ to C₂₀ fluoroalkyl group, a C₁ to C₂₀ perfluoroalkyl group(C_(n)F_(2n+1)), a C₁ to C₃₀ linear or branched alkoxy group, a C₃ toC₃₀ cycloalkoxy group, a C₂ to C₃₀ linear or branched alkoxyalkyl group,a C₄ to C₃₀ cycloalkoxyalkyl group, a cyano group, an amino group(—NRR′, wherein R and R′ are independently one of hydrogen and a C₁ toC₁₀ alkyl group), an amidino group (—C(═NH)NH₂), a nitro group (—NO₂),an amide group (—C(═O)N(H)R, wherein R is hydrogen or a C₁ to C₁₀ alkylgroup), an aldehyde group (—C(═O)H), a hydroxyl group (—OH), a sulfonylgroup (—S(═O)₂R, wherein R is one of hydrogen and a C₁ to C₁₀ alkylgroup), and a carbamate group (—NH₂C(═O)OR, wherein R is a C₁ to C₁₀alkyl group) instead of hydrogen, provided that the substituted atom'snormal valence is not exceeded.

According to example embodiments, a fused polycyclic heteroaromaticcompound may have a compact planar structure in which seven or morerings may be fused together in the following Chemical Formula 1.

In the above Chemical Formula 1,

Ar is a substituted or unsubstituted C₆ to C₃₀ aromatic cyclic group,

each of X¹ to X⁴ are independently one of O, S, Se, Te, N—R^(a), andCR^(b), wherein each of R^(a) and R^(b) are independently one ofhydrogen, a substituted or unsubstituted linear or branched C₁ to C₃₀alkyl group, for example, a substituted or unsubstituted linear orbranched C₁ to C₂₀ alkyl group, a substituted or unsubstituted C₇ to C₃₀arylalkyl group, for example, a substituted or unsubstituted C₇ to C₂₀arylalkyl group, a substituted or unsubstituted C₆ to C₃₀ aryl group,for example, a substituted or unsubstituted C₆ to C₂₀ aryl group, asubstituted or unsubstituted C₁ to C₃₀ alkoxy group, for example, asubstituted or unsubstituted C₁ to C₂₀ alkoxy group, a substituted orunsubstituted C₆ to C₃₀ aryloxy group, for example, a substituted orunsubstituted C₆ to C₂₀ aryloxy group (—OR¹¹, wherein R¹¹ is asubstituted or unsubstituted C₆ to C₃₀ aryl group, for example, asubstituted or unsubstituted C₆ to C₂₀ aryl group), a substituted orunsubstituted C₄ to C₃₀ cycloalkyl group, for example, a substituted orunsubstituted C₄ to C₂₀ cycloalkyl group, a substituted or unsubstitutedC₄ to C₃₀ cycloalkyloxy group, for example, a substituted orunsubstituted C₄ to C₂₀ cycloalkyloxy group (−OR¹², wherein R¹² is asubstituted or unsubstituted C₄ to C₃₀ cycloalkyl group, for example, asubstituted or unsubstituted C₄ to C₂₀ cycloalkyl group), a substitutedor unsubstituted C₂ to C₃₀ heteroaryl group, for example, a substitutedor unsubstituted C₂ to C₂₀ heteroaryl group, an acyl group (—C(═O)R¹³,wherein R¹³ is a substituted or unsubstituted C₁ to C₃₀ alkyl group, forexample, a C₁ to C₂₀ alkyl group), a sulfonyl group (—S(═O)₂R¹⁴, whereinR¹⁴ is a substituted or unsubstituted C₁ to C₃₀ alkyl group, forexample, a C₁ to C₂₀ alkyl group), and a carbamate group (—NHC(═O)OR¹⁵,wherein R¹⁵ is a substituted or unsubstituted C₁ to C₃₀ alkyl group, forexample, a substituted or unsubstituted C₁ to C₂₀ alkyl group),

at least one of X¹ and X² is selected from O, S, Se, Te, and N—R^(a), atleast one of X³ and X⁴ is selected from O, S, Se, Te, and N—R^(a),

each of X⁵ and X⁶ are independently one of O, S, Se, Te, N—R^(a), andCR^(b)R^(c) wherein each of R^(a) to R^(c) are independently one ofhydrogen, a substituted or unsubstituted linear or branched C₁ to C₃₀alkyl group, for example, a substituted or unsubstituted linear orbranched C₁ to C₂₀ alkyl group, a substituted or unsubstituted C₇ to C₃₀arylalkyl group, for example, a substituted or unsubstituted C₇ to C₂₀arylalkyl group, a substituted or unsubstituted C₆ to C₃₀ aryl group,for example, a substituted or unsubstituted C₆ to C₂₀ aryl group, asubstituted or unsubstituted C₁ to C₃₀ alkoxy group, for example, asubstituted or unsubstituted C₁ to C₂₀ alkoxy group, a substituted orunsubstituted C₆ to C₃₀ aryloxy group, for example, a substituted orunsubstituted C₆ to C₂₀ aryloxy group (—OR¹¹, wherein R¹¹ is asubstituted or unsubstituted C₆ to C₃₀ aryl group, for example, a C₆ toC₂₀ aryl group), a substituted or unsubstituted C₄ to C₃₀ cycloalkylgroup, for example, a substituted or unsubstituted C₄ to C₂₀ cycloalkylgroup, a substituted or unsubstituted C₄ to C₃₀ cycloalkyloxy group, forexample, a substituted or unsubstituted C₄ to C₂₀ cycloalkyloxy group(−OR¹², wherein R¹² is a substituted or unsubstituted C₄ to C₃₀cycloalkyl group, for example, a substituted or unsubstituted C₄ to C₂₀cycloalkyl group), a substituted or unsubstituted C₂ to C₃₀ heteroarylgroup, for example, a substituted or unsubstituted C₂ to C₂₀ heteroarylgroup, an acyl group (—C(═O)R¹³, wherein R¹³ is a substituted orunsubstituted C₁ to C₃₀ alkyl group, for example, a substituted orunsubstituted C₁ to C₂₀ alkyl group), a sulfonyl group (—S(═O)₂R¹⁴,wherein R¹⁴ is a substituted or unsubstituted C₁ to C₃₀ alkyl group, forexample, a substituted or unsubstituted C₁ to C₂₀ alkyl group), and acarbamate group (—NHC(═O)OR¹⁵, wherein R¹⁵ is a substituted orunsubstituted C₁ to C₃₀ alkyl group, for example, a substituted orunsubstituted C₁ to C₂₀ alkyl group), and

each of R¹ to R⁶ are independently one of hydrogen, halogen, asubstituted or unsubstituted linear or branched C₁ to C₃₀ alkyl group, asubstituted or unsubstituted linear or branched C₂ to C₃₀ alkenyl group,a substituted or unsubstituted linear or branched C₂ to C₃₀ alkynylgroup, for example, a substituted or unsubstituted linear or branched C₂to C₂₀ alkynyl group, a substituted or unsubstituted C₇ to C₃₀ arylalkylgroup, for example, a substituted or unsubstituted C₇ to C₂₀ arylalkylgroup, a substituted or unsubstituted C₂ to C₃₀ heteroarylalkyl group,for example, a substituted or unsubstituted C₂ to C₂₀ heteroarylalkylgroup, a substituted or unsubstituted C₂ to C₃₀ alkylheteroaryl group,for example, a substituted or unsubstituted C₂ to C₂₀ alkylheteroarylgroup, a substituted or unsubstituted C₅ to C₃₀ cycloalkyl group, forexample, a substituted or unsubstituted C₅ to C₂₀ cycloalkyl group, asubstituted or unsubstituted C₂ to C₃₀ heterocycloalkyl group, forexample, a substituted or unsubstituted C₂ to C₂₀ heterocycloalkylgroup, a substituted or unsubstituted C₆ to C₃₀ aryl group, for example,a substituted or unsubstituted C₆ to C₂₀ aryl group, and a substitutedor unsubstituted C₂ to C₃₀ heteroaryl group, for example, a substitutedor unsubstituted C₂ to C₂₀ heteroaryl group.

The fused polycyclic heteroaromatic compounds represented by the aboveChemical Formula 1 have a structure in which seven or more aromaticrings and heteroaromatic rings are fused. By having a compact planarmolecular structure, the fused polycyclic heteroaromatic compound has auniform and stable oxidation potential when applied to an actual deviceand shows higher charge mobility because the intermolecular packing andstacking are improved. Thereby, the fused polycyclic heteroaromaticcompounds may be more easily synthesized to be effectively applied to asemiconductor material and/or an electron transporting material. Inother words, benzene rings are positioned at both sides in the center oftwo rings containing X⁵ and X⁶ linked by an aromatic ring (Ar), and anX¹ and X²-containing hetero-ring and an X³ and X⁴-containing hetero-ringare condensed with the benzene rings in Chemical Formula 1, and therebythe conjugation structure is enlarged and the intermolecular interactionis enhanced.

In addition, by positioning a hetero-ring between benzene rings, thesolubility of the fused polycyclic heteroaromatic compound for theorganic solvent may be improved. By introducing a C₁₀ to C₃₀ longaliphatic chain group (e.g., a substituted or unsubstituted C₁₀ to C₃₀alkyl group or a substituted or unsubstituted C₁₀ to C₃₀ alkenyl group)into R¹ to R⁶, solubility of the fused polycyclic heteroaromaticcompound for the organic solvent may be improved. Due to the solubilityimprovement, the fused polycyclic heteroaromatic compound may be simplycoated by a solution process at room temperature as well as in adeposition process, and the thin film may be formed in a relatively widearea so the processibility and the workability are improved.

In the above Chemical Formula 1, the same atom at each of X¹ and X⁴, andX² and X³ may be positioned symmetrically to each other and thereforethe packing or stacking characteristics may be enhanced.

In the above Chemical Formula 1, one of X¹ and X² and one of X³ and X⁴may be a sulfur atom (S).

In the above Chemical Formula 1 Ar may be a substituted or unsubstitutedbenzene, a substituted or unsubstituted naphthalene, or a substituted orunsubstituted anthracene.

The fused polycyclic heteroaromatic compound may be one of the fusedpolycyclic heteroaromatic compounds represented by the followingChemical Formulae 1A to 1G.

In the above Chemical Formulae 1A to 1G,

X¹, X², X³, X⁴, X⁵, X⁶, R¹, R², R³, R⁴, R⁵, and R⁶ are the same as inChemical Formula 1,

each of R¹⁰⁰ to R¹⁰² are independently one of hydrogen, halogen (—F,—Cl, —Br or —I), a substituted or unsubstituted linear or branched C₁ toC₃₀ alkyl group, a substituted or unsubstituted linear or branched C₂ toC₃₀ alkenyl group, a substituted or unsubstituted linear or branched C₂to C₃₀ alkynyl group, a substituted or unsubstituted C₇ to C₃₀ arylalkylgroup, a substituted or unsubstituted C₂ to C₃₀ heteroarylalkyl group, asubstituted or unsubstituted C₂ to C₃₀ alkylheteroaryl group, asubstituted or unsubstituted C₅ to C₃₀ cycloalkyl group, a substitutedor unsubstituted C₂ to C₃₀ heterocycloalkyl group, a substituted orunsubstituted C₆ to C₃₀ aryl group, and a substituted or unsubstitutedC₂ to C₃₀ heteroaryl group, and

x, y, and z are integers of 1 or 2.

In the above Chemical Formulae 1A to 1G, one of X¹ and X² and one of X³and X⁴ may be a sulfur atom (S).

Examples of the fused polycyclic heteroaromatic compound may include thefollowing compounds (1) to (12).

The reorganization energy of compounds (1), (2), (5), and (6) among thecompounds (1) to (12) is calculated by using the Gaussian 03 program inDFT B3PW91 6-311G+ (d,p) level, and the results are shown in thefollowing Table 1. For comparison, the reorganization energy of thefollowing compounds ref-1 and ref-2 is also shown in Table 1.

TABLE 1 ref-1

ref-2

Reorganization E_(HOMO) E_(LUMO) ΔE Energy Compound (eV) (eV) (eV) (eV)Compound ref-1 −5.61 −1.76 3.84 0.135 Compound ref-2 −5.57 −1.99 3.570.162 Compound 1 −5.69 −1.93 3.75 0.095 Compound 2 −5.69 −2.10 3.590.096 Compound 5 −5.68 −1.89 3.79 0.086 Compound 6 −5.66 −2.04 3.620.105

As shown in Table 1, compounds (1), (2), (5), and (6) have lowerreorganization energies than compounds ref-1 and ref-2. From theresults, the compounds (1), (2), (5), and (6) are expected to haveimproved charge mobility compared with the compounds ref-1 and ref-2.

The fused polycyclic heteroaromatic compound according to exampleembodiments may be prepared according to a general method, for example,chemical or electrochemical oxidation synthesis, which is arepresentative method of polymerizing an aromatic compound or aheteroaromatic compound, or condensation polymerization using a compoundof an organic transition element (e.g., nickel or palladium).

For example, the compound of the above Chemical Formula 1 may beobtained by a cyclization reaction of an intermediate compound of thefollowing Chemical Formula 1-1. The cyclization reaction may beperformed by the method described in, for example, J. Org. Chem. 2005,70, 4502-4505.

In the above Chemical Formula 1-1,

X¹, X², X³, X⁴, X⁵, X⁶, R¹, R², R³, and R⁶ are the same as in theChemical Formula 1, Y¹ is an acyl group (—C(═O)R⁴, wherein R⁴ is thesame as in the Chemical Formula 1) or a halogen (e.g., —Br), and Y² isan acyl group (—C(═O)R⁵, wherein R⁵ is the same as in the ChemicalFormula 1) or a halogen (e.g., —Br). For example, the fused polycyclicheteroaromatic compound may be synthesized according to the followingReaction Scheme 1, but is not specifically limited thereto.

Reaction Scheme 1 may be performed using a heteroaromatic ring compoundsubstituted with bromine at about −78° C. to room temperature (about 23°C. to about 25° C.) while being exposed to air or a nitrogen atmosphere.The solvent may include the commonly used toluene, dimethyl formamide,N-methylpyrrolidinone, and/or tetrahydrofuran. The catalyst fordehydration in the last step may be an acidic catalyst (e.g., Amberlyst®15 (manufactured by Sigma-Aldrich)).

A person of ordinary skill in the art may adjust the molecular weight ofthe fused polycyclic heteroaromatic compound obtained from the synthesisaccording to example embodiments depending upon the usage and the case,for example, the molecular weight is about 350 to about 3000.

According to example embodiments, an organic thin film may include thefused polycyclic heteroaromatic compound and an electronic device mayinclude the organic thin film.

The organic thin film according to example embodiments may include thefused polycyclic heteroaromatic compound, and so may be applied to anorganic semiconductor layer for an electronic device, or a carriertransport layer (e.g., a channel layer). The electronic device includingthe same may have desirable electrical properties (e.g., higher chargemobility) as well as desirable processibility and workability.

The organic thin film may be manufactured by depositing the fusedpolycyclic heteroaromatic compound on a substrate according to thegeneral method or dissolving the fused polycyclic heteroaromaticcompound in an organic solvent and then coating the same at roomtemperature according to a solution process. If required, heatingtreatment may be performed after the deposition or coating process tofurther enhance the densification and uniformity of the thin film.

Particularly, the organic solvent may include at least one type ofgeneral organic solvent, for example, at least one type of an aliphatichydrocarbon solvent (e.g., hexane or heptane); an aromatic hydrocarbonsolvent (e.g., toluene, pyridine, quinoline, anisole, mesitylene orxylene); a ketone-based solvent (e.g., methyl isobutyl ketone,1-methyl-2-pyrrolidinone, cyclohexanone, or acetone); an ether-basedsolvent (e.g., tetrahydrofuran or isopropyl ether); an acetate-basedsolvent (e.g., ethyl acetate, butyl acetate, or propylene glycol methylether acetate); an alcohol-based solvent (e.g., isopropyl alcohol orbutanol); an amide-based solvent (e.g., dimethyl acetamide or dimethylformamide); a silicone-based solvent; and a mixture of foregoingsolvents. The amount of the fused polycyclic heteroaromatic compounddissolved in the organic solvent may be adequately selected anddetermined by a person of ordinary skill in the art, for example, in arange of about 0.01 wt % to about 50 wt % in the total solvent in viewof the solubility and a coating property.

The method of providing an organic thin film may include thermaldeposition, vacuum deposition, laser deposition, screen printing,printing, imprinting, spin casting, dipping, inkjetting, roll coating,flow coating, drop casting, spray coating, and/or roll printing, but isnot limited thereto. The heat treatment may be performed at about 80 toabout 250° C. for about 1 minute to about 2 hours, but is not limitedthereto.

The thickness of the organic thin film may be adjusted according to theusage and the case considering the types of the used compound andsolvent by a person of ordinary skill in the art, for example, in arange of about 200 Å to about 10,000 Å.

Examples of electronic devices including the organic thin film as acarrier transport layer may include a transistor, an organic lightemitting diode (OLED), a photovoltaic device, a solar cell, a laserdevice, a memory, and/or a sensor, and the organic thin film may beapplied to each device according to the general process commonly knownin the art.

For example, the transistor includes a gate electrode disposed on asubstrate; a source electrode and a drain electrode facing each otherand defining a channel region; an insulation layer electricallyinsulating the source electrode and drain electrode and the gateelectrode; and an active layer including the fused polycyclicheteroaromatic compound formed in the channel region.

The active layer may be obtained by depositing the fused polycyclicheteroaromatic compound, or applying a composition including the fusedpolycyclic heteroaromatic compound to a solution process (e.g., screenprinting, printing, spin coating, dipping, or ink jetting). When theactive layer is formed by the solution process, the process cost may bereduced, and a relatively wide area device may be effectivelymanufactured.

FIGS. 1 and 2 are schematic cross-sectional views showing a transistoraccording to example embodiments. The transistor according to exampleembodiments may be a thin film transistor. The thin film transistor maybe a thin film having a thickness of several nanometers to severalmicrons.

Referring to FIG. 1, a transistor 10 may include a substrate 12, a gateelectrode 14 disposed on the substrate, and an insulation layer 16covering the gate electrode 14. On the insulation layer 16, a sourceelectrode 17 a and a drain electrode 17 b defining a channel region maybe provided, and an active layer 18 may be provided in the channelregion. The active layer 18 may include the fused polycyclicheteroaromatic compound.

Referring to FIG. 2, a transistor 20 may include a source electrode 27 aand a drain electrode 27 b defining a channel region and that are formedon a substrate 22, and an active layer 28 formed on the channel region.The active layer 28 may include the fused polycyclic heteroaromaticcompound. An insulation layer 26 may be formed to cover the sourceelectrode 27 a, the drain electrode 27 b, and the active layer 28, and agate electrode 24 may be formed thereon.

The substrates 12 and 22 may include an inorganic material, an organicmaterial, or a composite of an inorganic material and an organicmaterial. The organic material may include, for example, a plastic(e.g., polyethylene naphthalate (PEN), polyethylene terephthalate (PET),polycarbonate, polyvinyl alcohol, polyacrylate, polyimide,polynorbornene, and polyethersulfone (PES)), and the inorganic materialmay include, for example, glass or metal.

In addition, the gate electrodes 14 and 24, source electrodes 17 a and27 a, and drain electrodes 17 b and 27 b may include a generally-usedmetal, for example, gold (Au), silver (Ag), aluminum (Al), nickel (Ni),or indium tin oxide (ITO), but are not limited thereto.

The insulation layers 16 and 26 may include a generally-used insulatorhaving a high dielectric constant, for example, a ferroelectricinsulator (e.g., Ba_(0.33)Sr_(0.66)TiO₃ (BST, barium strontiumtitanate), Al₂O₃, Ta₂O₅, La₂O₅, Y₂O₃, and/or TiO₂); an inorganicinsulator (e.g., PbZr_(0.33)Ti_(0.66)O₃ (PZT) Bi₄Ti₃O₁₂, BaMgF₄,SrBi₂(TaNb)₂O₉, Ba(ZrTi)O₃ (BZT), BaTiO₃, SrTiO₃, SiO₂, SiN_(x) (x isdetermined depending on valence of Si), and/or AlON (aluminumoxynitride)); or an organic insulator (e.g., polyimide, benzocyclobutene(BCB), parylene, polyacrylate, polyvinyl alcohol, and/orpolyvinylphenol), but are not limited thereto. Although it is notmentioned above, the inorganic insulator disclosed in U.S. Pat. No.5,946,551 and the organic insulator disclosed in U.S. Pat. No. 6,232,157may be used for the insulation layers 16 and 26.

Hereinafter, the embodiments are illustrated in more detail withreference to examples. However, the following are example embodimentsand are not limiting.

Example 1 Preparation of Fused Polycyclic Heteroaromatic Compound

The fused polycyclic heteroaromatic compound is synthesized as shown inthe following Reaction Scheme 2.

Synthesis of Compound 1:

Benzodithiophene (5.29 g, 28 mmol) is dissolved in 100 mL of dry THF(tetrahydrofuran), the resultant is added to 100 mL of an anhydrousdiethyl ether solution including butyl lithium (25 mL of 2.5 M in hexanesolution) cooled at 0° C. in a dropwise fashion, a temperature isincreased slowly, and the resultant is agitated at room temperature for2 hours. 3-bromo-thieno[3,2:b]thiophene-2-aldehyde (12 g, 62 mmol) isadded to the turbid solution in a dropwise fashion and is agitatedovernight. 100 ml of an ammonium chloride saturated aqueous solution isadded thereto, precipitated materials are filtered, and the resultant iswashed with water and diethyl ether to obtain a compound 1 (yield: 70%).

¹H NMR (300 MHz, CDCl₃): δ ppm 8.11 (d, 2H), 7.32 (d, 2H), 7.27 (d, 2H),6.98 (d, 2H), 6.47 (d, 2H), 2.79 (d, 2H); ¹³CNMR (75.5 MHz, CDCl₃): 6ppm 146.7, 140.7, 137.2, 137.1, 130.1, 126.0, 120.8, 117.2, 109.0, 68.6.

Synthesis of Compound 2:

The diol compound 1 (4.66 g, 8.15 mmole) is dissolved in 400 mL ofdichloromethane and ZnI₂ (8.3 g, 26 mmole) and NaCNBH₃ (7.2 g, 114mmole) are slowly added thereto. The resulting mixture is agitated atroom temperature for 24 hours, and then passes through a Celite pad. Thefiltered resultant is washed with an ammonium chloride saturatedsolution and water, respectively, dried with MgSO₄, and concentratedunder reduced pressure to obtain yellow oil. The yellow oil is purifiedwith a silica chromatography to obtain a compound 2 (yield: 77%).

¹H NMR (300 MHz, CDCl₃): δ ppm 8.02 (s, 2H), 7.20 (d, 2H), 7.07 (d, 2H),6.96 (d, 2H), 4.38 (s, 4H).

Synthesis of Compound 3:

THF solution (50 mL) including the compound 2 (1.4 g, 2.6 mmole)dissolved therein is added to a THF solution (50 mL) including t-butyllithium (1.7M, 4.5 mL, 7.7 mmole) cooled to −78° C., in a dropwisefashion. The resultant is agitated at −78° C. for about 30 minutes, andDMF (1 mL) is added followed by agitating for about 1 hour. Water ispoured thereto to complete a reaction, 100 mL of ethyl acetate is added,the resultant is washed with water and brine, and an organic layer isdried with MgSO₄, and concentrated under reduced pressure to obtaincolorless oil. The colorless oil is purified with a silicachromatography to obtain a compound 3 (yield: 60%).

¹H NMR (300 MHz, CDCl₃): δ ppm 10.1 (s, 2H), 8.04 (s, 2H), 7.45 (d, 2H),7.19 (d, 2H), 7.10 (s, 2H), 4.80 (s, 4H); ¹³C NMR (75.5 MHz, CDCl₃): 6ppm 184.7, 152.7, 142.8, 137.3, 137.2, 136.9, 128.2, 124.2, 121.5,116.4, 29.5.

Synthesis of Compound 4:

The compound 3 (0.35 g) is dissolved in 30 mL of benzene, Amberlyst® 15(manufactured by Sigma-Aldrich) (0.5 g) is added thereto, the mixture isagitated while refluxing and water is removed using a Dean-Stark trap.After 24 hours, a yellow solid is precipitated. After a temperature isdecreased into room temperature, Amberlyst® 15 is precipitated,suspended materials are removed using a filter to obtain a compound 4 asa yellow solid (yield: 60%).

Maldi-MS spectrum (Ultraflex III TOF/TOF 200 mass spectrometer, BrukerCorporation) of the compound 4 is shown in FIG. 3.

Example 2 Manufacture of Organic Thin Film Transistor Using FusedPolycyclic Heteroaromatic Compound

A silicon substrate covered with a 3000 Å silicon oxide film is rinsedwith isopropyl alcohol for 10 minutes

The rinsed silicon substrate is treated with oxygen plasma, dipped in aoctadecyl trichlorosilane solution that is diluted to a 5 mMconcentration in hexane, for 30 minutes, is rinsed with hexane andethanol, baked at 120° C. for 30 minutes, and washed with an ultrasonicwave in a chloroform solution. The washed silicon substrate is dried andthe fused polycyclic heteroaromatic compound 4 according to Example 1 isapplied at a thickness of 700 Å using a vacuum thermal deposition. Gold(Au) as a source-drain electrode is sputtered at a thickness of 1000 Åthereon to fabricate an OTFT device.

Current transfer characteristics of the OTFT device according to Example2 is measured using a semiconductor characterization system (KEITHLEY,4200-SCS) and the results are shown in FIG. 4. As shown in FIG. 4, theOTFT device according to Example 2 has improved current transfercharacteristics.

While this disclosure has been described in connection with what ispresently considered to be practical example embodiments, it is to beunderstood that the inventive concepts are not limited to the disclosedembodiments, but, on the contrary, are intended to cover variousmodifications and equivalent arrangements included within the spirit andscope of the appended claims.

What is claimed is:
 1. A fused polycyclic heteroaromatic compoundcomprising a structural unit represented by the following ChemicalFormula 1:

wherein, in the above Chemical Formula 1, Ar is a substituted orunsubstituted C₆ to C₃₀ aromatic cyclic group, each of X¹ to X⁴ areindependently one of O, S, Se, Te, N—R^(a), and CR^(b), wherein each ofR^(a) and R^(b) are independently one of hydrogen, a substituted orunsubstituted linear or branched C₁ to C₃₀ alkyl group, a substituted orunsubstituted C₇ to C₃₀ arylalkyl group, a substituted or unsubstitutedC₆ to C₃₀ aryl group, a substituted or unsubstituted C₁ to C₃₀ alkoxygroup, a substituted or unsubstituted C₆ to C₃₀ aryloxy group (—OR¹¹,wherein R¹¹ is a substituted or unsubstituted C₆ to C₃₀ aryl group), asubstituted or unsubstituted C₄ to C₃₀ cycloalkyl group, a substitutedor unsubstituted C₄ to C₃₀ cycloalkyloxy group (−OR¹², wherein R¹² is asubstituted or unsubstituted C₄ to C₃₀ cycloalkyl group), a substitutedor unsubstituted C₂ to C₃₀ heteroaryl group, an acyl group (—C(═O)R¹³,wherein R¹³ is a substituted or unsubstituted C₁ to C₃₀ alkyl group), asulfonyl group (—S(═O)₂R¹⁴, wherein R¹⁴ is a substituted orunsubstituted C₁ to C₃₀ alkyl group) and a carbamate group(—NHC(═O)OR¹⁵, wherein R¹⁵ is a substituted or unsubstituted C₁ to C₃₀alkyl group), at least one of X¹ and X² is selected from O, S, Se, Te,and N—R^(a), at least one of X³ and X⁴ is selected from O, S, Se, Te,and N—R^(a), each of X⁵ and X⁶ are independently one of O, S, Se, Te,N—R^(a), and CR^(b)R^(c) wherein each of R^(a) to R^(c) areindependently one of hydrogen, a substituted or unsubstituted linear orbranched C₁ to C₃₀ alkyl group, a substituted or unsubstituted C₇ to C₃₀arylalkyl group, a substituted or unsubstituted C₆ to C₃₀ aryl group, asubstituted or unsubstituted C₁ to C₃₀ alkoxy group, a substituted orunsubstituted C₆ to C₃₀ aryloxy group (—OR¹¹, wherein R¹¹ is asubstituted or unsubstituted C₆ to C₃₀ aryl group), a substituted orunsubstituted C₄ to C₃₀ cycloalkyl group, a substituted or unsubstitutedC₄ to C₃₀ cycloalkyloxy group (−OR¹², wherein R¹² is a substituted orunsubstituted C₄ to C₃₀ cycloalkyl group), a substituted orunsubstituted C₂ to C₃₀ heteroaryl group, an acyl group (—C(═O)R¹³,wherein R¹³ is a substituted or unsubstituted C₁ to C₃₀ alkyl group), asulfonyl group (—S(═O)₂R¹⁴, wherein R¹⁴ is a substituted orunsubstituted C₁ to C₃₀ alkyl group) and a carbamate group(—NHC(═O)OR¹⁵, wherein R¹⁵ is a substituted or unsubstituted C₁ to C₃₀alkyl group), and each of R¹ to R⁶ are independently one of hydrogen, ahalogen (—F, —Cl, —Br or —I), a substituted or unsubstituted linear orbranched C₁ to C₃₀ alkyl group, a substituted or unsubstituted linear orbranched C₂ to C₃₀ alkenyl group, a substituted or unsubstituted linearor branched C₂ to C₃₀ alkynyl group, a substituted or unsubstituted C₇to C₃₀ arylalkyl group, a substituted or unsubstituted C₂ to C₃₀heteroarylalkyl group, a substituted or unsubstituted C₂ to C₃₀alkylheteroaryl group, a substituted or unsubstituted C₅ to C₃₀cycloalkyl group, a substituted or unsubstituted C₂ to C₃₀heterocycloalkyl group, a substituted or unsubstituted C₆ to C₃₀ arylgroup, and a substituted or unsubstituted C₂ to C₃₀ heteroaryl group. 2.The fused polycyclic heteroaromatic compound of claim 1, wherein thefused polycyclic heteroaromatic compound is represented by the followingChemical Formula 1A:

wherein, in the above Chemical Formula 1A, each of X¹ to X⁴ areindependently one of O, S, Se, Te, N—R^(a), and CR^(b), wherein each ofR^(a) and R^(b) are independently one of hydrogen, a substituted orunsubstituted linear or branched C₁ to C₃₀ alkyl group, a substituted orunsubstituted C₇ to C₃₀ arylalkyl group, a substituted or unsubstitutedC₆ to C₃₀ aryl group, a substituted or unsubstituted C₁ to C₃₀ alkoxygroup, a substituted or unsubstituted C₆ to C₃₀ aryloxy group (—OR¹¹,wherein R¹¹ is a substituted or unsubstituted C₆ to C₃₀ aryl group), asubstituted or unsubstituted C₄ to C₃₀ cycloalkyl group, a substitutedor unsubstituted C₄ to C₃₀ cycloalkyloxy group (−OR¹², wherein R¹² is asubstituted or unsubstituted C₄ to C₃₀ cycloalkyl group), a substitutedor unsubstituted C₂ to C₃₀ heteroaryl group, an acyl group (—C(═O)R¹³,wherein R¹³ is a substituted or unsubstituted C₁ to C₃₀ alkyl group), asulfonyl group (—S(═O)₂R¹⁴, wherein R¹⁴ is a substituted orunsubstituted C₁ to C₃₀ alkyl group) and a carbamate group(—NHC(═O)OR¹⁵, wherein R¹⁵ is a substituted or unsubstituted C₁ to C₃₀alkyl group), at least one of X¹ and X² is selected from O, S, Se, Te,and N—R^(a), at least one of X³ and X⁴ is selected from O, S, Se, Te,and N—R^(a) each of X⁵ and X⁶ are independently one of O, S, Se, Te,N—R^(a), and CR^(b)R^(c) wherein each of R^(a) to R^(c) areindependently one of hydrogen, a substituted or unsubstituted linear orbranched C₁ to C₃₀ alkyl group, a substituted or unsubstituted C₇ to C₃₀arylalkyl group, a substituted or unsubstituted C₆ to C₃₀ aryl group, asubstituted or unsubstituted C₁ to C₃₀ alkoxy group, a substituted orunsubstituted C₆ to C₃₀ aryloxy group (—OR¹¹, wherein R¹¹ is asubstituted or unsubstituted C₆ to C₃₀ aryl group), a substituted orunsubstituted C₄ to C₃₀ cycloalkyl group, a substituted or unsubstitutedC₄ to C₃₀ cycloalkyloxy group (−OR¹², wherein R¹² is a substituted orunsubstituted C₄ to C₃₀ cycloalkyl group), a substituted orunsubstituted C₂ to C₃₀ heteroaryl group, an acyl group (—C(═O)R¹³,wherein R¹³ is a substituted or unsubstituted C₁ to C₃₀ alkyl group), asulfonyl group (—S(═O)_(2R14), wherein R¹⁴ is a substituted orunsubstituted C₁ to C₃₀ alkyl group) and a carbamate group(—NHC(═O)OR¹⁵, wherein R¹⁵ is a substituted or unsubstituted C₁ to C₃₀alkyl group), each of R¹ to R⁶ are independently one of hydrogen, ahalogen (—F, —Cl, —Br or —I), a substituted or unsubstituted linear orbranched C₁ to C₃₀ alkyl group, a substituted or unsubstituted linear orbranched C₂ to C₃₀ alkenyl group, a substituted or unsubstituted linearor branched C₂ to C₃₀ alkynyl group, a substituted or unsubstituted C₇to C₃₀ arylalkyl group, a substituted or unsubstituted C₂ to C₃₀heteroarylalkyl group, a substituted or unsubstituted C₂ to C₃₀alkylheteroaryl group, a substituted or unsubstituted C₅ to C₃₀cycloalkyl group, a substituted or unsubstituted C₂ to C₃₀heterocycloalkyl group, a substituted or unsubstituted C₆ to C₃₀ arylgroup, and a substituted or unsubstituted C₂ to C₃₀ heteroaryl group,R¹⁰⁰ is hydrogen, a halogen (—F, —Cl, —Br or —I), a substituted orunsubstituted linear or branched C₁ to C₃₀ alkyl group, a substituted orunsubstituted linear or branched C₂ to C₃₀ alkenyl group, a substitutedor unsubstituted linear or branched C₂ to C₃₀ alkynyl group, asubstituted or unsubstituted C₇ to C₃₀ arylalkyl group, a substituted orunsubstituted C₂ to C₃₀ heteroarylalkyl group, a substituted orunsubstituted C₂ to C₃₀ alkylheteroaryl group, a substituted orunsubstituted C₅ to C₃₀ cycloalkyl group, a substituted or unsubstitutedC₂ to C₃₀ heterocycloalkyl group, a substituted or unsubstituted C₆ toC₃₀ aryl group, or a substituted or unsubstituted C₂ to C₃₀ heteroarylgroup, and x is an integer of 1 or
 2. 3. The fused polycyclicheteroaromatic compound of claim 2, wherein, in Chemical Formula 1A,each of R¹ to R⁶ are independently one of a substituted or unsubstitutedlinear or branched C₁ to C₃₀ alkyl group, a substituted or unsubstitutedlinear or branched C₂ to C₃₀ alkenyl group, a substituted orunsubstituted linear or branched C₂ to C₃₀ alkynyl group, a substitutedor unsubstituted C₇ to C₃₀ arylalkyl group, a substituted orunsubstituted C₂ to C₃₀ heteroarylalkyl group, a substituted orunsubstituted C₂ to C₃₀ alkylheteroaryl group, a substituted orunsubstituted C₅ to C₃₀ cycloalkyl group, a substituted or unsubstitutedC₂ to C₃₀ heterocycloalkyl group, a substituted or unsubstituted C₆ toC₃₀ aryl group, and a substituted or unsubstituted C₂ to C₃₀ heteroarylgroup.
 4. The fused polycyclic heteroaromatic compound of claim 2,wherein, in Chemical Formula 1A, one of X¹ and X² and one of X³ and X⁴are sulfur (S).
 5. The fused polycyclic heteroaromatic compound of claim1, wherein the fused polycyclic heteroaromatic compound is representedby one of the following Chemical Formulae 1B to 1D:

wherein, in the above Chemical Formulae 1B to 1D, each of X¹ to X⁴ areindependently one of O, S, Se, Te, N—R^(a), and CR^(b), wherein each ofR^(a) and R^(b) are independently one of hydrogen, a substituted orunsubstituted linear or branched C₁ to C₃₀ alkyl group, a substituted orunsubstituted C₇ to C₃₀ arylalkyl group, a substituted or unsubstitutedC₆ to C₃₀ aryl group, a substituted or unsubstituted C₁ to C₃₀ alkoxygroup, a substituted or unsubstituted C₆ to C₃₀ aryloxy group (—OR¹¹,wherein R¹¹ is a substituted or unsubstituted C₆ to C₃₀ aryl group), asubstituted or unsubstituted C₄ to C₃₀ cycloalkyl group, a substitutedor unsubstituted C₄ to C₃₀ cycloalkyloxy group (−OR¹², wherein R¹² is asubstituted or unsubstituted C₄ to C₃₀ cycloalkyl group), a substitutedor unsubstituted C₂ to C₃₀ heteroaryl group, an acyl group (—C(═O)R¹³,wherein R¹³ is a substituted or unsubstituted C₁ to C₃₀ alkyl group), asulfonyl group (—S(═O)₂R¹⁴, wherein R¹⁴ is a substituted orunsubstituted C₁ to C₃₀ alkyl group) and a carbamate group(—NHC(═O)OR¹⁵, wherein R¹⁵ is a substituted or unsubstituted C₁ to C₃₀alkyl group), at least one of X¹ and X² is selected from O, S, Se, Te,and N—R^(a), at least one of X³ and X⁴ is selected from O, S, Se, Te,and N—R^(a) each of X⁵ and X⁶ are independently one of O, S, Se, Te,N—R^(a), and CR^(b)R^(c) wherein each of R^(a) to R^(c) areindependently one of hydrogen, a substituted or unsubstituted linear orbranched C₁ to C₃₀ alkyl group, a substituted or unsubstituted C₇ to C₃₀arylalkyl group, a substituted or unsubstituted C₆ to C₃₀ aryl group, asubstituted or unsubstituted C₁ to C₃₀ alkoxy group, a substituted orunsubstituted C₆ to C₃₀ aryloxy group (—OR¹¹, wherein R¹¹ is asubstituted or unsubstituted C₆ to C₃₀ aryl group), a substituted orunsubstituted C₄ to C₃₀ cycloalkyl group, a substituted or unsubstitutedC₄ to C₃₀ cycloalkyloxy group (−OR¹², wherein R¹² is a substituted orunsubstituted C₄ to C₃₀ cycloalkyl group), a substituted orunsubstituted C₂ to C₃₀ heteroaryl group, an acyl group (—C(═O)R¹³,wherein R¹³ is a substituted or unsubstituted C₁ to C₃₀ alkyl group), asulfonyl group (—S(═O)₂R¹⁴, wherein R¹⁴ is a substituted orunsubstituted C₁ to C₃₀ alkyl group) and a carbamate group(—NHC(═O)OR¹⁶, wherein R¹⁵ is a substituted or unsubstituted C₁ to C₃₀alkyl group), each of R¹ to R⁶ are independently one of hydrogen, ahalogen (—F, —Cl, —Br or —I), a substituted or unsubstituted linear orbranched C₁ to C₃₀ alkyl group, a substituted or unsubstituted linear orbranched C₂ to C₃₀ alkenyl group, a substituted or unsubstituted linearor branched C₂ to C₃₀ alkynyl group, a substituted or unsubstituted C₇to C₃₀ arylalkyl group, a substituted or unsubstituted C₂ to C₃₀heteroarylalkyl group, a substituted or unsubstituted C₂ to C₃₀alkylheteroaryl group, a substituted or unsubstituted C₅ to C₃₀cycloalkyl group, a substituted or unsubstituted C₂ to C₃₀heterocycloalkyl group, a substituted or unsubstituted C₆ to C₃₀ arylgroup, and a substituted or unsubstituted C₂ to C₃₀ heteroaryl groupeach of R¹⁰⁰ and R¹⁰¹ are independently one of hydrogen, a halogen (—F,—Cl, —Br or —I), a substituted or unsubstituted linear or branched C₁ toC₃₀ alkyl group, a substituted or unsubstituted linear or branched C₂ toC₃₀ alkenyl group, a substituted or unsubstituted linear or branched C₂to C₃₀ alkynyl group, a substituted or unsubstituted C₇ to C₃₀ arylalkylgroup, a substituted or unsubstituted C₂ to C₃₀ heteroarylalkyl group, asubstituted or unsubstituted C₂ to C₃₀ alkylheteroaryl group, asubstituted or unsubstituted C₅ to C₃₀ cycloalkyl group, a substitutedor unsubstituted C₂ to C₃₀ heterocycloalkyl group, a substituted orunsubstituted C₆ to C₃₀ aryl group, and a substituted or unsubstitutedC₂ to C₃₀ heteroaryl group, and x and y are integers of 1 or
 2. 6. Thefused polycyclic heteroaromatic compound of claim 5, wherein, inChemical Formulae 1B to 1D, each of R¹ to R⁶ are independently one of asubstituted or unsubstituted linear or branched C₁ to C₃₀ alkyl group, asubstituted or unsubstituted linear or branched C₂ to C₃₀ alkenyl group,a substituted or unsubstituted linear or branched C₂ to C₃₀ alkynylgroup, a substituted or unsubstituted C₇ to C₃₀ arylalkyl group, asubstituted or unsubstituted C₂ to C₃₀ heteroarylalkyl group, asubstituted or unsubstituted C₂ to C₃₀ alkylheteroaryl group, asubstituted or unsubstituted C₅ to C₃₀ cycloalkyl group, a substitutedor unsubstituted C₂ to C₃₀ heterocycloalkyl group, a substituted orunsubstituted C₆ to C₃₀ aryl group, and a substituted or unsubstitutedC₂ to C₃₀ heteroaryl group.
 7. The fused polycyclic heteroaromaticcompound of claim 5, wherein, in Chemical Formulae 1B to 1D, one of X¹and X² and one of X³ and X⁴ are sulfur (S).
 8. The fused polycyclicheteroaromatic compound of claim 1, wherein the fused polycyclicheteroaromatic compound is represented by one of the following ChemicalFormulae 1E to 1G:

wherein, in the above Chemical Formulae 1 E to 1G, each of X¹ to X⁴ areindependently one of O, S, Se, Te, N—R^(a), and CR^(b), wherein each ofR^(a) and R^(b) are independently one of hydrogen, a substituted orunsubstituted linear or branched C₁ to C₃₀ alkyl group, a substituted orunsubstituted C₇ to C₃₀ arylalkyl group, a substituted or unsubstitutedC₆ to C₃₀ aryl group, a substituted or unsubstituted C₁ to C₃₀ alkoxygroup, a substituted or unsubstituted C₆ to C₃₀ aryloxy group (—OR¹¹,wherein R¹¹ is a substituted or unsubstituted C₆ to C₃₀ aryl group), asubstituted or unsubstituted C₄ to C₃₀ cycloalkyl group, a substitutedor unsubstituted C₄ to C₃₀ cycloalkyloxy group (−OR¹², wherein R¹² is asubstituted or unsubstituted C₄ to C₃₀ cycloalkyl group), a substitutedor unsubstituted C₂ to C₃₀ heteroaryl group, an acyl group (—C(═O)R¹³,wherein R¹³ is a substituted or unsubstituted C₁ to C₃₀ alkyl group), asulfonyl group (—S(═O)₂R¹⁴, wherein R¹⁴ is a substituted orunsubstituted C₁ to C₃₀ alkyl group) and a carbamate group(—NHC(═O)OR¹⁵, wherein R¹⁵ is a substituted or unsubstituted C₁ to C₃₀alkyl group), at least one of X¹ and X² is selected from O, S, Se, Te,and N—R^(a), at least one of X³ and X⁴ is selected from O, S, Se, Te,and N—R^(a), each of X⁵ and X⁶ are independently one of O, S, Se, Te,N—R^(a), and CR^(b)R^(c) wherein each of R^(a) to R^(c) areindependently one of hydrogen, a substituted or unsubstituted linear orbranched C₁ to C₃₀ alkyl group, a substituted or unsubstituted C₇ to C₃₀arylalkyl group, a substituted or unsubstituted C₆ to C₃₀ aryl group, asubstituted or unsubstituted C₁ to C₃₀ alkoxy group, a substituted orunsubstituted C₆ to C₃₀ aryloxy group (—OR¹¹, wherein R¹¹ is asubstituted or unsubstituted C₆ to C₃₀ aryl group), a substituted orunsubstituted C₄ to C₃₀ cycloalkyl group, a substituted or unsubstitutedC₄ to C₃₀ cycloalkyloxy group (−OR¹², wherein R¹² is a substituted orunsubstituted C₄ to C₃₀ cycloalkyl group), a substituted orunsubstituted C₂ to C₃₀ heteroaryl group, an acyl group (—C(═O)R¹³,wherein R¹³ is a substituted or unsubstituted C₁ to C₃₀ alkyl group), asulfonyl group (—S(═O)₂R¹⁴, wherein R¹⁴ is a substituted orunsubstituted C₁ to C₃₀ alkyl group) and a carbamate group(—NHC(═O)OR¹⁵, wherein R¹⁵ is a substituted or unsubstituted C₁ to C₃₀alkyl group), and each of R¹ to R⁶ are independently one of hydrogen, ahalogen (—F, —Cl, —Br or —I), a substituted or unsubstituted linear orbranched C₁ to C₃₀ alkyl group, a substituted or unsubstituted linear orbranched C₂ to C₃₀ alkenyl group, a substituted or unsubstituted linearor branched C₂ to C₃₀ alkynyl group, a substituted or unsubstituted C₇to C₃₀ arylalkyl group, a substituted or unsubstituted C₂ to C₃₀heteroarylalkyl group, a substituted or unsubstituted C₂ to C₃₀alkylheteroaryl group, a substituted or unsubstituted C₅ to C₃₀cycloalkyl group, a substituted or unsubstituted C₂ to C₃₀heterocycloalkyl group, a substituted or unsubstituted C₆ to C₃₀ arylgroup, and a substituted or unsubstituted C₂ to C₃₀ heteroaryl group.each of R¹⁰⁰ to R¹⁰² are independently one of hydrogen, a halogen (—F,—Cl, —Br or —I), a substituted or unsubstituted linear or branched C₁ toC₃₀ alkyl group, a substituted or unsubstituted linear or branched C₂ toC₃₀ alkenyl group, a substituted or unsubstituted linear or branched C₂to C₃₀ alkynyl group, a substituted or unsubstituted C₇ to C₃₀ arylalkylgroup, a substituted or unsubstituted C₂ to C₃₀ heteroarylalkyl group, asubstituted or unsubstituted C₂ to C₃₀ alkylheteroaryl group, asubstituted or unsubstituted C₅ to C₃₀ cycloalkyl group, a substitutedor unsubstituted C₂ to C₃₀ heterocycloalkyl group, a substituted orunsubstituted C₆ to C₃₀ aryl group, and a substituted or unsubstitutedC₂ to C₃₀ heteroaryl group, and x, y, and z are integers of 1 or
 2. 9.The fused polycyclic heteroaromatic compound of claim 8, wherein, inChemical Formulae 1E to 1G, each of R¹ to R⁶ are independently one of asubstituted or unsubstituted linear or branched C₁ to C₃₀ alkyl group, asubstituted or unsubstituted linear or branched C₂ to C₃₀ alkenyl group,a substituted or unsubstituted linear or branched C₂ to C₃₀ alkynylgroup, a substituted or unsubstituted C₇ to C₃₀ arylalkyl group, asubstituted or unsubstituted C₂ to C₃₀ heteroarylalkyl group, asubstituted or unsubstituted C₂ to C₃₀ alkylheteroaryl group, asubstituted or unsubstituted C₅ to C₃₀ cycloalkyl group, a substitutedor unsubstituted C₂ to C₃₀ heterocycloalkyl group, a substituted orunsubstituted C₆ to C₃₀ aryl group, and a substituted or unsubstitutedC₂ to C₃₀ heteroaryl group.
 10. The fused polycyclic heteroaromaticcompound of claim 8, wherein, in Chemical Formulae 1E to 1G, one of X¹and X² and one of X³ and X⁴ are sulfur (S).
 11. The fused polycyclicheteroaromatic compound of claim 1, wherein, in Chemical Formula 1, anatom of each of X¹ and X⁴, and X² and X³ is positioned symmetrically toeach other.
 12. The fused polycyclic heteroaromatic compound of claim 1,wherein, in Chemical Formula 1, one of X¹ and X² and one of X³ and X⁴are sulfur (S).
 13. The fused polycyclic heteroaromatic compound ofclaim 1, wherein, in Chemical Formula 1, Ar is one of a substituted orunsubstituted benzene, a substituted or unsubstituted naphthalene, and asubstituted or unsubstituted anthracene.
 14. The fused polycyclicheteroaromatic compound of claim 1, wherein the fused polycyclicheteroaromatic compound has an average molecular weight of about 350 toabout
 3000. 15. The fused polycyclic heteroaromatic compound of claim 1,wherein, in Chemical Formula 1, each of R¹ to R⁶ are independently oneof a substituted or unsubstituted linear or branched C₁ to C₃₀ alkylgroup, a substituted or unsubstituted linear or branched C₂ to C₃₀alkenyl group, a substituted or unsubstituted linear or branched C₂ toC₃₀ alkynyl group, a substituted or unsubstituted C₇ to C₃₀ arylalkylgroup, a substituted or unsubstituted C₂ to C₃₀ heteroarylalkyl group, asubstituted or unsubstituted C₂ to C₃₀ alkylheteroaryl group, asubstituted or unsubstituted C₅ to C₃₀ cycloalkyl group, a substitutedor unsubstituted C₂ to C₃₀ heterocycloalkyl group, a substituted orunsubstituted C₆ to C₃₀ aryl group, and a substituted or unsubstitutedC₂ to C₃₀ heteroaryl group.
 16. An organic thin film comprising thefused polycyclic heteroaromatic compound according to claim
 1. 17. Anelectronic device comprising the fused polycyclic heteroaromaticcompound according to claim
 1. 18. The electronic device of claim 17,wherein the electronic device is one of a transistor, an organic lightemitting diode (OLED), a photovoltaic device, a solar cell, a laserdevice, a memory, and a sensor.
 19. The electronic device of claim 17,further comprising: a transistor including an active layer formed of thefused polycyclic heteroaromatic compound in a channel region.